| Identification | More | [Name]
Spermidine | [CAS]
124-20-9 | [Synonyms]
1,8-DIAMINO-4-AZAOCTANE
N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE
N-(3-AMINOPROPYL)-1,4-BUTANDIAMINE
N-[3-AMINOPROPYL]-1,4-BUTANEDIAMINE
N-(3-AMINOPROPYL)-1,4-DIAMINOBUTANE
OMEGA-AMINOBUTYL-OMEGA-AMINOPROPYLAMINE
SPERMIDINE
SPERMIDINE FREE BASE
1,5,10-triazadecane
n-(3-aminopropyl)-4-butanediamine
n-(3-aminopropyl)-4-diaminobutane
4-azaoctamethylenediamine
N-(3-Aminopropyl)-1,4-diaminobutane~1,8-Diamino-4-azaoctane
Spermidine N-(3-Aminopropyl)-1,4-butanediamine
SPERMIDINE FREE BASE CELL CULTURE*TESTED
SPERMIDINE, FOR MOLECULAR BIOLOGY
SPERMIDINE FREE BASE MOLECULAR BIOLOGY*R EAGENT
Spermidine 0.1 M Solution
1,4-Butanediamine, N-(3-aminopropyl)-
N-(3-aminopropyl)butane-1,4-diamine | [EINECS(EC#)]
204-689-0 | [Molecular Formula]
C7H19N3 | [MDL Number]
MFCD00008229 | [Molecular Weight]
145.25 | [MOL File]
124-20-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless clear liquid | [Melting point ]
23-25 °C
| [Boiling point ]
128-130 °C (14 mmHg)
| [density ]
1.00 g/mL at 20 °C
| [refractive index ]
n20/D 1.479(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
H2O: 1 M at 20 °C, clear, colorless
| [form ]
Liquid After Melting | [pka]
10.53±0.19(Predicted) | [color ]
Clear colorless | [Specific Gravity]
0.925 | [Odor]
Ichtyal, ammoniacal | [PH]
12.0-13.5 (25℃, 1M in H2O) | [Stability:]
Stable, but air-sensitive and very hygroscopic-store under argon. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. | [Water Solubility ]
Miscible with water, ethanol and ether. | [Sensitive ]
Air Sensitive | [λmax]
λ: 260 nm Amax: 0.1
λ: 280 nm Amax: 0.05 | [Merck ]
14,8742 | [BRN ]
1698591 | [InChIKey]
ATHGHQPFGPMSJY-UHFFFAOYSA-N | [CAS DataBase Reference]
124-20-9(CAS DataBase Reference) | [EPA Substance Registry System]
124-20-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 2735 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
EJ7000000
| [F ]
3-10-34 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29212900 |
| Hazard Information | Back Directory | [Description]
Spermidine is an endogenous polyamine.1 It is formed from putrescine by spermidine synthase. Spermidine (25 μM) inhibits the activity of the human inward-rectifying potassium channel Kir2.3 in a patch-clamp assay.2 It induces autophagy in HeLa cells when used at a concentration of 100 μM and increases the lifespan of D. melanogaster, yeast, and C. elegans.3 Spermidine (30 mM in the drinking water) reduces demyelination of the optic nerve and disease severity in a mouse model of experimental autoimmune encephalomyelitis (EAE).4 It reduces increases in blood pressure, left ventricular posterior wall thickness, and heart weight in salt-sensitive Dahl rats fed a high-salt diet, a model of hypertension-induced congestive heart failure.5 Formulations containing spermidine have been used as dietary supplements. | [Chemical Properties]
Colorless clear liquid | [Occurrence]
Spermidine is found in fresh green pepper, wheat germ, cauliflower, broccoli, mushrooms, and a variety of cheeses. Even higher amounts are found in soybean products such as natto, shitake mushrooms, amaranth grain and durian. Some of these ingredients are particularly common in a Mediterranean diet, which may explain why some believe eating like the Spanish can prolong your life. | [Source]
Spermidine is found in fresh green pepper, wheat germ, cauliflower, broccoli, mushrooms, and a variety of cheeses. Even higher amounts are found in soybean products such as natto, shitake mushrooms, amaranth grain and durian. Some of these ingredients are particularly common in a Mediterranean diet, which may explain why some believe eating like the Spanish can prolong your life. | [Uses]
Spermidine is a biogenic polyamine formed from putrescine. Spermidine is a precursor of Spermine. Spermidine is essential for both normal and neoplastic tissue growth. | [Application]
Spermidine has been used:
in the preparation of 5x transcription buffer
in the treatment of double-stranded RNA along with other reagents to increase the uptake of dsRNA by nematodes
as a standard in the analytical study of rat brain polyamines (185) | [Definition]
ChEBI: A triamine that is the 1,5,10-triaza derivative of decane. | [Preparation]
The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.
Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of Spermidine
J. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011
DOI: 10.1590/S0103-50532011000100011 | [benefits]
Spermidine is crucial in the process of cell renewal. As old cells die, other cannibalise them and put molecules to use in building new cells. As we get older our natural levels of spermidine decrease reducing the ability of our cells to renew and repair themselves.
Spermidine has also been shown to reduce the risks of some forms of cancer, preserve telomere length and, if taken regularly enough over a long period of time, can expand lifespan. It also maintains autophagy in T cells and may improve vaccine protection in older adults. Research shows that spermidine inhibits five of the nine hallmarks of aging.
Spermidine plays a key role in maintaining cells’ membrane potential and controlling intracellular pH and volume.
Studies also suggest it can reduce the risk of cardiovascular disease and improve cognition. Spermidine has a neuroprotective effect against neuron damage caused by inflammation and ischemia and oxidative stress.
Spermidine is a relatively new player on the scene, but is being increasingly used in supplement products. It is not a silver bullet, and will not offer a miracle extension of your life expectancy on you own. However, it does mimic some of the other life extending interventions such as calorie restriction in keeping cells healthier, improving brain function and keeping your body ticking over for a little bit longer. | [General Description]
Spermidine is a naturally occurring polyamine compound commonly found in food. It is essential for cell growth and survival. | [Biological Activity]
Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase. Spermidine (25 μM) inhibits the activity of the human inward-rectifying potassium channel Kir2.3 in a patch- clamp assay. It induces autophagy in HeLa cells when used at a concentration of 100 μM and increases the lifespan of D. melanogaster, yeast, and C. elegans. Spermidine (30 mM in the drinking water) reduces demyelination of the optic nerve and disease severity in a mouse model of experimental autoimmune encephalomyelitis (EAE). It reduces increases in blood pressure, left ventricular posterior wall thickness, and heart weight in salt-sensitive Dahl rats fed a high-salt diet, a model of hypertension-induced congestive heart failure. Formulations containing spermidine have been used as dietary supplements. | [Biochem/physiol Actions]
Spermidine is a naturally occurring polyamine. It is associated with various cellular functions. It is responsible for the condensation and aggregation of DNA in aqueous solution. Spermidine is known to extend lifespan via epigenetic modifications, induction of cell death and inhibition of necrosis.Spermidine 0.1M solution is an additive screening solution of Additive Screening Kit. Additive Screen kit is designed to allow rapid and convenient evaluation of additives and their ability to influence the crystallization of the sample. The Additive Kit provides a tool for refining crystallization conditions. | [Side effects]
There are currently no known side effects from the intake of spermidine. Countless trials and scientific studies have already been conducted on this subject and the results show the full tolerance of this natural ingredient by our body. Because spermidine is not only absorbed by our daily food, but our body itself produces spermidine. | [storage]
Store at -20°C | [Purification Methods]
It is a strong base with an alkylamine odour and absorbs CO2 from the atmosphere. It is purified by shaking with solid K2CO3 or NaOH, decanting and distilling from K2CO3 in a vacuum. Store it in the dark under N2. [Beilstein 4 IV 1300.] | [Mode of action]
Spermidine's main mechanism of action is its ability to induce autophagy, a self-preservation process which clears out toxic, damaged and dysfunctional cells, resulting in lower levels of inflammation in the body. Autophagy is the main mechanism of spermidine in delaying aging and prolonging the lifespan. In addition, spermidine exerts its effects through other mechanisms, including anti-inflammation, histone acetylation reduction, lipid metabolism and regulation of cell growth and signaling pathways. | [References]
Madeo, F., Eisenberg, T., Pietrocola, F., et al. Spermidine in health and disease. Science 359(6374), eaan2788 (2018).
Lopatin, A.N., Makhina, E.N., and Nichols, C.G. Potassium channel block by cytoplasmic polyamines as the mechanism of intrinsic rectification. Nature 372(6504), 366-369 (1994).
Eisenberg, T., Knauer, H., Schauer, A., et al. Induction of autophagy by spermidine promotes longevity. Nat. Cell Biol. 11(11), 1305-1314 (2009).
Guo, X., Harada, C., Namekata, K., et al. Spermidine alleviates severity of murine experimental autoimmune encephalomyelitis. Invest. Ophthalmol. Vis. Sci. 52(5), 2696-2703 (2011).
Eisenberg, T., Abdellatif, M., Schroeder, S., et al. Cardioprotection and lifespan extension by the natural polyamine spermidine. Nat. Med. 22(12), 1428-1438 (2016). |
|
|